Violet-red dye and process of making same.



UNrreo STATES Erica ATENT OSCAR BALLY, OF MANNHEIM, GERMANY, ASSIGNOR TO THE BADISGHE ANILIN AND SODA FABRIK, OF LUDWIGSHAFEN, GERMANY.

VIOLET-RED DYE AND PROCESS OF MAKING SAME.

SPECIFICATION forming part Of Letters Patent No. 659,565, dated October 9, 1900.

Application filed June 24,1899. Serial No. 721,761. (S ecimens) To all whom it ntay concern:

Be it known that I, OSCAR BALLY, doctor of philosophy, acitizen of the Swiss Republic, residing at Mannheim, in the Grand Duchy of Baden and Empire of Germany, have invented new and useful Improvements in the Manufacture of Violet-Red Coloring-Matter for Wool, (for which applications have been filed in Germany, dated December 9, 1898, No. B. 23,887; in England,dated April 11, 1899, No. 7,591, and in France, dated May 4, 1899, No. 276,452,) of which the following is a specification.

It is known that if l.o-di-ortho-nitro-anthraquinone be boiled with anilin a product is obtained which crystallizes in deep-red needles and dissolves in hot alcohol, giving purple solutions. This was first described by Bottger and Petersen in 1873. (See Berichte ofthe German Chemical Society,Vol. 6, p. 16.) Ten years later, in 1883, the body was more accurately described by Romer. (See Berichzfc ofthe Ger-man Chemical Society, Vol. 16, p. 363.) This body is intensely colored. It dissolves in such solvents as glacial acetic acid, benzene,and the like, yieldingintenselyred solutions; but it possesses no affinity for textile fibers and cannot be regarded as a dyestuff in a practical sense, andno means of converting it into a useful product has been described. Analogous bodies can be obtained if the dinitro-anthraquinone be treated with other aromatic amins instead of with anilin, and the bodies so obtained I term di-alphyldiamido-anthraquinone. In United States Letters Patent Nos. 631,605 and 631,606, of August 22, 1899, I have already described the utilization of these bodies for the production of halogen derivatives and of coloring-matters of the anthracene series.

My present invention relates to the manufacture of wool-coloring matters of the said di-alphyl diamido-anthraquinone by sulfonation.

Different results are obtained, according to whether the snlfonation be conducted energetically or moderately. Upon moderate sulfonation with concentrated sulfuric acid at a temperature not exceeding 100 a coloringmatter is obtained which is readily soluble in hot water, but can be readily precipitated from its solution by common salt. The shades obtained upon wool with coloring-matter obtained in this way are violet-red in color; but if the di-alphyl-diamido-anthraquinone be energetically sulfonated, say, with fuming sulfuric acid containing twenty per cent. free anhydride a coloring matter is obtained which is soluble in hot or cold water and cannot readily be precipitated from its solution with common salt or potassium chlorid. Such coloring-matter dies wool, yielding yellowish shades of red.

In the present application for Letters Patent I desire to claim the violet-red coloringmatters referred to generically, and specifically the violet-red coloring-matter which can be obtained from di-anilido-anthraquinone, and do not claim the yellow-red coloring-inatters which constitute the subject-matter of an application, Serial No. 721,762, of even date herewith.

The following example will serve to illustrate the manner in which my invention can be carried into practical efiect:

Example: Mix together one hundred (100) parts of 1.5-di-anilido-anthraquinonethat is to say, the condensation product obtained from 1.4t-di-ortho nitro anthraquinone and anilinand one thousand (1,000) parts of concentrated sulfuric acid, (containing about ninety-six per cent. H 80 Heat the mixture to a temperature of about from 80 to 100 centigrade. Take tests from time to time and continue heating until a test portion is readily soluble in hot water. Then allow the melt to cool and pour it into water. Add a little common salt, which will be sufficient to precipitate the coloring-matter. Filter-,press, and dry.

My new coloring-matters possess a chocolate-brown appearance. They are readily soluble in hot Water,giving red solutions. The addition of sodium carbonate or caustic soda to the aqueous solution does not change its color.

The coloring-matter dissolves in alcohol and in warm anilin, giving a cherry-red solution.

In concentrated sulfuric acid this specific coloring-mat ter yields a dirty-brown solution.

Now what I claim is 1. The violet-red coloring-matter which can be obtained from di-alphyl-di-an1ido-anthrm quinone by treatment with concent-zratedisu-l: f uric acidat a temperature below 100, which is readily soluble in hot water, but can be readily precipitated from its solutions by common salt, and whose aqueous solution is red and remains unchanged in color-by the-addition of sodium carbonate or caustic soda-,andiwhioh is soluble in alcohol and in warm aniline, all substantially as described.

2. The new violet-red'coloring-matterwhichcan be obtained from 1.5-di-anilido-anthraquinone by treatment with concentrated sulfuric acid, at a temperature below'100, which is readily soluble in hot water givingaired' sol-- lution, which is unchanged in color by the addition ofi sodium carbonate or caustic soda, but from which it can be readily precipitated by common salt, and which is soluble in alcohol and warm anilin giving cherry-red 'solutions, and which gives dirty-brown solutions in ccnccntirated sul'fil ri'nacid, all substantially :as described;

In testimony whereof I have hereunto set my hand in the presence of two subscribing 25 witnesses:

OSCAR BALLY. Witnesses:

Gwsrzw EUT'DEN-BERGER, GEORG KOERNER. 

